Diethylamine → (S)-2-(5-(diethylamino)-2-nitrophenyl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isonicotinamide

HRID 625436Notes

Reaction equation

F[C:2]1[CH:3]=[CH:4][C:5]([N+:27]([O-:29])=[O:28])=[C:6]([C:8]2[CH:9]=[C:10]([CH:24]=[CH:25][N:26]=2)[C:11]([NH:13][C@@H:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)=[O:12])[CH:7]=1.[CH2:30]([NH:32][CH2:33][CH3:34])[CH3:31].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:30]([N:32]([CH2:33][CH3:34])[C:2]1[CH:3]=[CH:4][C:5]([N+:27]([O-:29])=[O:28])=[C:6]([C:8]2[CH:9]=[C:10]([CH:24]=[CH:25][N:26]=2)[C:11]([NH:13][C@@H:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][CH2:16][CH2:15]2)=[O:12])[CH:7]=1)[CH3:31]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (S)-2-(5-fluoro-2-nitrophenyl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)isonicotinamide (12.77 mmol, 5 g), diethylamine (25.55 mmol, 1.87 g), and K2CO3 (31.93 mmol, 4.41 g) in DMF (30 mL) was stirred at 60° C. overnight. The mixture was diluted with ethyl acetate, and the resulting solution was washed with water (2×), and then with brine. The solution was dried (Na2SO4) and the solvent was removed at reduced pressure. The residue was purified by chromatography on silica gel to give a yellow solid. (4.73 g, 83%).

Workup

washthe resulting solution was washed with water (2×)
dry with materialThe solution was dried (Na2SO4)
customthe solvent was removed at reduced pressure
customThe residue was purified by chromatography on silica gel
customto give a yellow solid

Sources & evidence

ORD record: ord-12a2f743d3fb4590b57086393ee12eee
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09301951B2

Reaction notes

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